Structure-retention correlation of isomeric bile acids in inclusion high-performance liquid chromatography with methyl beta-cyclodextrin.
The structure-retention correlation of various C24 bile acid isomers was studied by the addition of methyl beta-cyclodextrin (Me-beta-CD) to mobile phases in reversed-phase high-performance liquid chromatography (HPLC). The compounds examined include a series of monosubstituted bile acids related to cholanoic acids differing from one another in the position and configuration of an oxygen-containing function (hydroxyl or oxo group) at the position C-3, C-6, C-7, or C-12 and the stereochemistry of the A/B-ring fusion (trans 5 alpha-H and cis 5 beta-H) in the steroid nucleus. The inclusion HPLC with Me-beta-CD was also applied to biologically important 4 beta- and 6-hydroxylated bile acids substituted by three to four hydroxyl groups in the 5 beta-steroid nucleus. These bile acid samples were converted into their fluorescence prelabeled 24-pyrenacyl ester derivatives and chromatographed on a Capcell Pak C18 column eluted with methanol-water mixtures in the presence or absence of 5 mM Me-beta-CD. The effects of Me-beta-CD on the retentions of each compound were correlated quantitatively to the decreasing rate of capacity factors and the relative strength of host-guest interactions. On the basis of the retention data, specific and nonspecific hydrogen-bonding interactions between the bile acids and the Me-beta-CD were discussed.
Momose
T
T
College of Engineering, Nihon University, Fukushima, Japan.
Yamaguchi
Y
Y
Iida
T
T
Goto
J
J
Nambara
T
T
D001647:Bile Acids and Salts / Q000737:chemistry* / Q000302:isolation & purification; D002635:Chenodeoxycholic Acid / Q000737:chemistry; D019826:Cholic Acid; D002793:Cholic Acids / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry; D003840:Deoxycholic Acid / Q000737:chemistry; D004951:Esterification; D005456:Fluorescent Dyes; D006860:Hydrogen Bonding; D006900:Hydroxylation; D007202:Indicators and Reagents; D008095:Lithocholic Acid / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014580:Ursodeoxycholic Acid / Q000737:chemistry; D047392:beta-Cyclodextrins
D001647:Bile Acids and Salts; D002793:Cholic Acids; D003505:Cyclodextrins; D005456:Fluorescent Dyes; D007202:Indicators and Reagents; D047392:beta-Cyclodextrins; C108732:methyl-beta-cyclodextrin; D003840:Deoxycholic Acid; D002635:Chenodeoxycholic Acid; D008095:Lithocholic Acid; D014580:Ursodeoxycholic Acid; D019826:Cholic Acid